Ethanol → 1-(3-(Benzyloxy)pyridin-2-yl)thiourea

Participants

Reaction Steps

A 1 L round-bottomed flask was charged with 1-benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thiourea (44.4 g, 122 mmol), potassium carbonate (20.3 g, 147 mmol), and EtOH (400 mL). The reaction mixture was heated to reflux overnight, then cooled, poured into water (900 mL) and filtered to afford 1-(3-(benzyloxy)pyridin-2-yl)thiourea (34.6 g) as a yellow solid. 1H NMR (CDCl3) δ 11.01 (s, 1H), 8.69 (s, 1H), 7.78 (d, 1H), 7.44-7.34 (m, 5H), 7.16 (d, 1H), 7.09 (bs, 1H), 6.91 (dd, 1H), 5.16 (s, 2H). LCMS (25 to 95) Rt=2.06 min (apci) m/z=260 (M+H).

Provenance & Evidence